Meeting online contacts offline can be considered both as a risk-taking behavior and as an opportunity to expand one's social circle. This study distinguishes between specific types of meetings, whether with ‘friends of friends’, ‘complete strangers’ or ‘both’, and examines the role of individual psychological factors (sensation seeking, selfefficacy and psychological difficulties) together with structural societal factors (agentic and communal life strategies - locus of control and importance of friends) while controlling for age, gender and personal Internet use. Data from the Euro Kids Online II project dealing with children and adolescents who reported being in touch via Internet with people whom they didn't know personally and indicated whether or not they had met them offline were compounded with data from the European Values Study for societal factors and analyzed through two-level multinomial logistic regression. The odds of engaging in meeting online contacts offline increase with higher sensation seeking, self-efficacy, psychological difficulties, and age, and decrease with higher importance of friends. Types of meetings were found to vary with age and level of sensation-seeking. The results are discussed with regard to risk-taking in adolescence, safety of meeting types, models of sociability, and personal agency.